Simon has been with NPR for over three decades, beginning in 1977 as Chicago bureau chief,[8] and his career encompasses other types of media as well.

His books include Home and Away: Memoir of a Fan (2000); Jackie Robinson and the Integration of Baseball (2002); Baby, We Were Meant for Each Other: In Praise of Adoption (2010), about his experiences adopting two daughters; and the novels Pretty Birds (2005) and Windy City: A Novel of Politics (2008).[11]

On November 15, 2014, at the beginning of an interview for Weekend Edition Saturday, Bill Cosby and his wife Camille declined to respond to the accusations of sexual assault against Cosby when Simon gave them the opportunity. As narrated by Simon in the interview, Cosby only shook his head no. The rest of the interview focused on the couple's loan of their 62-piece African art collection for an exhibition in Washington, D.C.[16]

Simon has won every major award in broadcasting, including the Peabody and the Emmy, and has received numerous honorary degrees.[12] In May 2010, he was awarded an Honorary Doctor of Humane Letters degree by Willamette University, where he was that year's commencement speaker.[17] He was named a Lincoln Laureate in 2016 in the area of Business, Industry & Communications.[18]

Simon met French documentary filmmaker Caroline Richard during an NPR interview in 2000. They married on September 10, 2000, in a mixed-faith (Methodist, Quaker, and Jewish) service in Ridgefield, Connecticut, at the home of fashion designer Alexander Julian.[1] They have two daughters, both adopted as babies from China: Elise, in 2004,[19][20][21] and Lina, in 2007.[22] They consider themselves a Jewish family (Simon's father was Jewish and his mother was Irish Catholic).[8][20]

In 2006 Simon and his wife were contacted by police as part of the Alexander Litvinenko poisoning investigation. The family was staying at a hotel near the restaurant at the center of the poisoning incident, and had twice bought food there for their daughter Elise. The health of the family was not affected.[23]

In July 2013, in a groundbreaking use of social media, Simon began tweeting his emotions and conversations with his mother during her last days of life, which she spent in a hospital intensive-care unit. "I just realized: she once had to let me go into the big wide world. Now I have to let her go the same way", read one tweet. In March 2015, he published a memoir about her titled Unforgettable: A Son, a Mother, and the Lessons of a Lifetime.[24]